DE1793852C2 - 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten - Google Patents

4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten

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Publication number
DE1793852C2
DE1793852C2 DE1793852A DE1793852A DE1793852C2 DE 1793852 C2 DE1793852 C2 DE 1793852C2 DE 1793852 A DE1793852 A DE 1793852A DE 1793852 A DE1793852 A DE 1793852A DE 1793852 C2 DE1793852 C2 DE 1793852C2
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DE
Germany
Prior art keywords
taste
methyl
thiazole
propionyl
butyrylthiazole
Prior art date
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Expired
Application number
DE1793852A
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English (en)
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DE1793852B1 (de
Inventor
I Flament
F Gautschi
I M Goldman
M Stoll
M Winter
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Firmenich SA
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Firmenich SA
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Application filed by Firmenich SA filed Critical Firmenich SA
Publication of DE1793852B1 publication Critical patent/DE1793852B1/de
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Publication of DE1793852C2 publication Critical patent/DE1793852C2/de
Expired legal-status Critical Current

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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid

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Description

C=O
(D
worin Ri einen Alkylrest mit 1 bis 3 Kohlenstoffatomen und Rj ein Wasserstoffatom oder die Methylgruppe bedeutet als Geschmacksstoffe in Getränken, Nahrungs- und Genußmitteln oder als Geschmacksstoffkomponenten in geschmacksverändernden Mitteln.
3. Ausführu.ngsform nach Anspruch 2, dadurch gekennzeichnet, daß man die Verbindungen der allgemeinen Forme! ! zum Aromatisieren von löslichen Kaffeeprodukten verwendet.
-s-
C=O
(I)
Die Erfindung betrifft die Verwendung von Thiazolcarbonylverbindungen der allgemeinen Formel
wo. in Ri einen Alkylrest mit I bis 3 Kohlenstoffatomen und R2 ein Wasserstoffatom oder die Methylgruppe bedeutet als Geschmacksstoffe in Getränken, Nahrungsund Genußmitteln oder als Geschmacksstoffkomponenten in geschmacksverändernden Mitteln.
Die Erfindung hat schließlich neue Thiazolcai bonylverbindungen zum Gegenstand, und zwar 4-Methyl-2-propionyl-thiazol und 4-Methyl-2-butyryl-lhiazol.
Unter »geschmacksverändernd« sind alle Vorgänge oder Behandlungen zu verstehen, durch welche geschmacksfreien bzw. geschmacksarmen Nahrungsmitteln und Getränken ein bestimmter Geschmack oder ein bestimmtes Aroma verliehen wird, oder durch welche der Geschmack von Nahrungsmitteln und Getränken verstärkt, verbessert, überdeckt, unterdrückt oder sonstwie in einer bestimmten Geschmacksrichtung verändert wird.
Die der Erfindung zu Grunde liegende Aufgabe bestand darin, die Auswahl der bisher zur Verfugung stehenden Geschmacksstoffe zu erweitern und dem Lebcnsmitteltcchniker neue und verfeinerte ivlittel in die Hand /u geben, um die von der Natur erzeugten Aromen auf synthetischem Wege besser nachahmen /11 können. Die Veränderung oder Verbesserung der geschmacklichen Eigenschaften von Nahrungsmitteln und Gelränken durch Verwendung von künstlichen Aromen mit genau reproduzierbaren (ieschmackseigenschaften und -qualitativ' nimmt in der Lebensmittelindustrie mehr und mehr .in llrdeutiing /11. seitdem fur die Ιτη.ιΙιπίπμ des Mensehen neue, bisher nicht verwendete Kohstoffe erschlossen werden, um der drohenden Verknappung der Nahrungsmittel in gewissen < iehielen des Lrdb.ills enIgegen ζυtreten
Es wurde gefunden, daß die oben beschriebenen Verbindungen entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und flüssiger Nahrungs- und Genußmittel oder Getränke im gewünschten Sinne zu verändern. Mittels der Erfindung können beispielsweise Produkte wie Fruchtsäfte, Gemüsesäfte, Milchprodukte, Kaffee-, Tee-, Kakao- und Schokoladeprodukte, Getreideflocken, Mehle, Konfiseriewaren, Fleischprodukte, Backwaren und Speiseeis geschmacklich verändert werden. Die Erfindung eignet sich insbesondere zur Verbesserung oder Verstärkung des Geschmackes von konservierten Lebensmitteln. Ganz besonders eignet sich die Erfindung zur Veränderung. Verbesserung oder Verstärkung der Geschmackseigenschaften von sogenannten löslichen Kafeeprodukten (im englischen Sprachgebrauch als »instant coffee« bezeichnet).
Anschließend folgen die unter die allgenKine Formel I fallenden Thiazolcarbonylverbindungen. Neben dem chemischen Namen jeder Verbindung ist ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben.
Für die neuen Verbindungen (abgekürzt »n. V.«) sind im Anschluß an die Aufzählung der Einzelverbindungen Herstellungsmethoden angegeben.
a. 4-Methyl-2-acetyl-thiazol Bull. 20, 702 (1953)
b. 4-Methyl-2-propionyI-thiazol n. V.
c. 5-Methyl-2-acetyl-thiazol Bull. 20, 702 (1953)
d. 4-Methyl-2-butyryl-thiazol n.V.
Die neuen Verbindungen dieser Stoffklasse können wie folgt hergestellt werden:
(1) b. 4-Methyl-2-propionyI-thiazol wurde nach der in Bull. 20, 702 (1953) beschriebenen Methode hergestellt, indem 4-Methyl-thiazol mit Äthylmagnesiumbromid umgesetzt und die als Zwischenprodukt gebildete Grignard-Verbindung mit Propionylchlorid acyliert wurde. Das Produkt wies einen Sdp. von 83-88°C/ 9 mm Hg auf.
(I) d. 4-Methyl-2-butyryl-thiazol wurde in der gleichen Weise wie die Verbindung (I) b. hergestellt, wobei jedoch Butyranhydrid als Acylierungsmittel verwendet wurde. Das Produkt wies einen Sdp. von 11O bis ll5°C/8mmHgauf.
Die organoleptische Bewertung der oben definierten Verbindungen wurde mittels Prüfmedioden A und B durchgeführt. Die Methode A diente dazu, den Eigengeschmack der einzelnen Substanzen zu ermitteln. Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methode B ermitlel' Es wurde insbesondere die gcschmacksverändernde Wirkung der Prüfsubstanzen (im folgenden »Geschmacksstoffe« genannt) auf Kaffeeprodukte und speziell auf sprühgetrocknete lösliche Kaffeepulver geprüft.
Methode A
Die Grsrhm.ickssloffc wurden in einer 61J1W)IgCn Zuckersinip Losung, bestehend auf Rohrzucker in Leitungswasser, gekostet. Die zu prüfenden Geschmacks stoffe wurden dem Sirup in Lorm von Losungen von I Gew.-"/» oder I (iew.%» in W/nigem Alkohol zugegeben Die Konzentration der Geschmacksstoffe im /uckersirup schwankte entsprechend der Geschmacks-
intensität zwischen 0,005 und 5 g pro 100 Liter Sirup, Proben des aromatisierten Sirups wurden einer Gruppe von Geschmacksprüfern vorgelegt Nach dem Kosten der Proben mußte jeder Prüfer eine Beschreibung des Geschmackes der einzelnen Geschmacksstoffe abgeben.
Methode B
Als Substrat für die Geschmacksprüfung wurde eine 135%ige Lösung eines im Handel erhältlichen, sprühgestrockneten Kaffeepulvers mit verhältnismäßig »flachem« Geschmack und Aroma in Quellwasser verwendet Die einzelnen Geschmacksstoffe wurden je einer Portion des Kaffeegetränkes mittels einer Mikrospritze in Mengen von 2 bis 150 Mikroliter zugegeben. Alle für die Zubereitung des Kaffeegetränkes, sowie die Aromatisierung, verwendeten Gefäße und sonstigen Geräte wurden peinlichst gesäubert Für die Geschmacksprüfung wurden mindestens 5 erfahrene Geschmacksprüfer eingesetzt Nach Zugabe der abgemessenen Menge der Geschmacksstofflösung wurde das Kaffeegetränk gut gerührt und sofort in eine Reihe von Tassen für die organoleptische Prüfung gegossen. Das Kosten des Getränkes wurde so rasch als möglich, auf jeden Fall nicht später als 15 Minuten nach der Zubereitung vorgenommen.
Die nur mit einer Kennzahl versehenen gefüllten Tassen wurden in einer Reihe autgestellt, wobei die erste Tasse eine nicht aromatisierte Vergleichsprobe des Kaffeegetränkes enthielt Die Geschmacksprüfer mußten feststellen, ob zwischen der Vergleichsprobe und den anderen Proben geschmacklich ein Unterschied bestand oder nicht Die Prüfer mußten ferner die Geschmacksunterschiede btschreib-n und charakterisieren.
' Die Resultate der organoleptische. Prüfung sind in der nachfolgenden Tabelle zusammengefaßt In der ersten Kolonne der Tabelle sind die Buchstaben der einzelnen Verbindungen innerhalb der genannten Stoffklasse angeführt Die zweite Kolonne verweist auf die angewendete Priifmethode. In der dritten Kolonne sind die verwendeten Mengen der Prüfsubstanzen in g pro 100 Liter Getränk (Zuckersirup oder Kaffeegetränk) angegeben.
Tabelle
Vcr- Ver Meng
! bin- such
i dung

a. 		A 2,0
b. A 3,0
C. A 0,5
C. B 0,034
d. A 3,0
Organoleptische Bewertung
anthranilisch. verbrannt
fruchtig, verbrannt
Geschmack verbrannter
Nüsse
toastartig; ungeröstete
Kaffeebohnen
grüner Grapefruitgeschmack
Die organoleptischen Eigenschaften weiterer Ver- «ι bindungen der allgemeinen Formel I gehen aus dem folgenden Vcrsuchsbcricht hervor:
Λ) 2-Acctyl-thiazol
i) 100 g 2-Amimiihiii/ol wurden bei OC zu 400 ecm 84"/oiger Phmphosiiure zugefügt. Die Rcaklionsmist'hiing wurde auf - 101X' abgekühlt, und unter griinillichem Rühren wurden 180 ecm 65%ige Salpetersäure und anschließend 90 g Natriumnitrit in 120 ecm Wasser eingetropft Die so erhaltene Reaktionsmischung wurde eine weitere Stunde bei - 10°C gerührt und schließlich
* bei derselben Temperatur gehalten. Die obige Mischung sowie eine Lösung aus 268 g Natriumbromid in 250 ecm Wasser wurden dann gleichzeitig zu einer kalten (-5"C) Lösung aus 325 g CuSO4 · 5 H3O in 600 ecm Wasser innerhalb von etwa 90 Minuten zuge-
Ki fügt und die Reaktionsmischung weitere 30 Minuten bei 00C gerührt Dann würde die obige Mischung mit einer 20%igen wäßrigen Natriumhydroxidlösung auf pH 7 neutralisiert und schließlich zur Bildung von etwa 3 I Destillat destilliert Das so erhaltene Material wurde
ι "> mit Natriumchlorid gesättigt, mit Äther extrahiert, über wasserfreiem Natriumsulfat getrocknet eingedampft und schließlich unter Bildung von 136 g (83% Ausbeute) 2-Bromthiazol mit einem Kp. 72—75°C/25 Torr destilliert
ii) 135 g 2-Bromthiazol in 200 ecm wasserfreiem Äther wurden zu einer Lösung aus 55,3 g Butyllithium in 532 ecm Hexan und 300 ecm wasserfreiem Äther (auf — 700C abgekühlt) innerhalb von etwa 45 Minuten zugefügt Nach weiterem, 90 Minuten langem Rühren
2Ί wurden 363 g Äthylacetat in 400 ecm wasserfreiem Äther zugefügt. Nachdem die Reaktionsmischung 4 Stunden bei Zimmertemperatur gehalten worden war, wurde sie auf 00C abgekühlt, mit 500 ecm 10%iger wäßriger HCI angesäuert, mit Natriumchlorid gesättigt
jo und schließlich mit Äther extrahiert. Nach Trocknen über wasserfreiem Natriumsulfat, Eindampfen und Destillieren erhielt man 78,6 g (75% Ausbeute) 2-Acetylthiazol mit einem Kp. 74ΧΓ/11 Torr.
MS: M + = 127 (43);
j-, m/e= 112 (30), 99 (41), 85 (13), 84 (10), 58 (35), 57
(18), 43 (100).
B) 2-Propionylthiazol
13,5 g 2-Bromthiazol, 55,8 ecm einer 1,55N Lösung aus Butyllithium in Hexan und 42 g Äthylpropionat wurden wie oben umgesetzt und lieferten nach Reinigung 8,7 g (72% Ausbeute) 2-Propionylthiazol mit einem Kp. 84XZ/10 Torr. IR (flüssiger Film): 1686 cm-'
MS:M^ = I41 (12);
m/e= 114 (11), 113 (92), 112 (100), 86 (12), 85 (31), 84 (21), 59 (13), 58 (32), 57 (84), 45 (8), 29 (71).
C) 2-Butyrylthiazol
I J,5g 2-Bromthiazol, 55,8 ecm einer 1.55N Lösung aus Butyllithium in Hexan und 47,8 g Äthylbutyrat wurden wie oben umgesetzt und lieferten nach Reinigung 8,9 g (70% Ausbeute) 2-Butyrylthiazol mit einem Kp. 91 bis93X:/1I Torr. IR (flüssiger Film): 1683 cm '
m/e = 140 (12), 127 (32). 113 (20), 112 (96), 99 (19), 86 (20), 85 (64), 84 (17), 71 (30), 59 (29), SS (30), 57 (28), 4J(IOO).
Die folgenden drei Verbindungen wurden /ur Dünn führung verschiedener Aroniiitcsts verwendet;
Verbindung Λ = 2-Acctyllhia/.ol
Verbindung Ii = 2-Propionylthia/ol
Verbindung C = nutyrylthia/.ol
1) Organoleptische Auswertung in Wasser
Dosis
(ppm)*)
Bemerkungen
Verb. Dosis
(ppm)
Bemerkungen
Dosis
(ppm)
Bemerkungen*)
Verb. Dosis
(ppm)
Bemerkungen*)
5) Verwendung der Verbindungen A, B und A als aromamodifizierende Bestandteile in einem Karamellaromapräparat
A 2,0 verbrannt, geröstet, Tiergeschmack;
an Haselnüsse erinnernd
B 2,0 geröstet; weniger Tiergeschmack und
stärker haselnußartig als A
C 2,0 frische Haselnüsse, fruchtiger Ge
schmack
*) =Teile pro Mill.
2) Aromatisierung von Salzwasser, d.h. 0,5%ige Natriumchloridlösung in Wasser
A 2,0 fleischiger Geschmack, an Roastbeef- ^
sauce erinnernd; geröstete Haselnüsse
B 2,0 gerösteter Fleischgeschmack; Hasel
nüsse
C 2,0 leicht fruchtig; an bestimmte Aspekte
des Kaffeegeschmacks erinnernd 2>
3) Aromatisierung von Roastbeef-sauce, hergestellt aus 45 g handelsüblichem Roastbeefsaucenpulver und 300 ecm Wasser
A 2,0 tierischer, fleischiger Geschmack; ver
stärkt den gerösteten Fleischcharak- j-, ter
B 2,0 tierischer, fleischiger Geschmack; ver
stärkt den gerösteten Fleischcharakter
C 3,0 leicht fruchtig, sauer; verleiht einen ·"'
butterartigen Geschmack
*) Diese Auswertung stammt von einem Gremium von Aromaexperten nach Vergleich mit einem unaromatisierten Material.
4) Aromatisierung von Milch
4Ί
a) Karamellgrundlage
Heliotropin
Äthylvanillin
Vanillin
Muskatnußöl
Äthylbutyrat
Lirnonenöl
Diacetyl
Süßorangenöl
Rhumäther
Äthylalkohol, 95%ig
Insgesamt
b) Karamellaromapräparate
Gew.-Tiile
30
40
300
10
250
350
1000
Nr. 1 Nr. 2 Gew.-Teiie
Nr. 3 Nr.
KarameligrunHl.
Verbindung A; 10%*)
Verbindung B; 10%
Verbindung C; 10%
Äthylalkohol 95%
Insgesamt
*) Lösung in Äthylalkohol.
100 100 100
- 25 - -
- - 25 -
- - 900 875 375
1000 1000 1000 1000
[)ann wurden die obigen vier Aromapräparate bis 4 in einer Menge von 1 g Aromapräparat pro 1 1 verdünntem Zuckersirup zum Aromatisieren des letzteren verwendet und die so aromatisierten Sirupe von einem Gremium von ^romaexperten wie: folgt bewertet:
A 2,0 gerostete Haselnüsse; leicht tierisch
B 2,0 geröstete Haselnüsse; kokosartig,
leicht tierisch
C 3,0 leicht fruchtig; butterartiger, cremiger
Geschmack
*) Diese Auswertung stammt von einem Gremium von Aromaexperten nach Vergleich mit einem unaromatisierten Material.
50
Sirup. typisch karamell, fruchtig, butter
aromatisiert artig
mit Nr. 1 geröstete Mandeln, geröstete Ha
selnüsse und leicht kokosartig
mit Nr. 2 dieselbe Aroma*irkung wie Nr. 2
fruchtig, an frische Haselnüsse er
mit Nr. 3 innernd
mit Nr. 4

Claims (2)

Patentansprüche:
1. 4-Methyl-2-propionyl-thiazol und 4-Methyl-2-butyryl-thiazol.
2. Verwendung von Thiazolcarbonylverbindungen der allgemeinen Formel
R,-
N R1
DE1793852A 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten Expired DE1793852C2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45234265A 1965-04-30 1965-04-30
US54306966A 1966-04-18 1966-04-18

Publications (2)

Publication Number Publication Date
DE1793852B1 DE1793852B1 (de) 1980-01-24
DE1793852C2 true DE1793852C2 (de) 1980-10-09

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Family Applications (12)

Application Number Title Priority Date Filing Date
DE1793851A Expired DE1793851C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen
DE1793847A Expired DE1793847C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793842A Expired DE1793842C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793848A Expired DE1793848C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793843A Expired DE1793843C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1695505A Expired DE1695505C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente

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Application Number Title Priority Date Filing Date
DE1793851A Expired DE1793851C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen
DE1793847A Expired DE1793847C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793842A Expired DE1793842C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793848A Expired DE1793848C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton

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DE1793843A Expired DE1793843C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1695505A Expired DE1695505C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente

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ID30544A (id) 1999-04-20 2001-12-20 Ajinomoto Kk Komposisi prekursor citarasa dan metode untuk melepaskan komponen citarasa
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JP5153195B2 (ja) * 2007-04-13 2013-02-27 長谷川香料株式会社 コーヒーの淹れたて感賦与剤
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DE1793847C3 (de) 1981-04-02
NL150316B (nl) 1976-08-16
JPS499747B1 (de) 1974-03-06
DE1793845B1 (de) 1979-10-31
SE373733B (de) 1975-02-17
DE1695505B2 (de) 1979-04-05
GB1156472A (en) 1969-06-25
BR6679143D0 (pt) 1973-09-11
SE377269B (de) 1975-06-30
SE373732B (de) 1975-02-17
DE1793843B1 (de) 1980-04-30
DE1793844B1 (de) 1979-10-31
SE373735B (de) 1975-02-17
DE1695505A1 (de) 1970-12-23
NL6605854A (de) 1966-10-31
JPS5412552B1 (de) 1979-05-23
DE1695505C3 (de) 1979-11-29
DE1793851C2 (de) 1982-07-01
DE1793852B1 (de) 1980-01-24
SE335463B (de) 1971-05-24
DK139012C (de) 1979-05-14
JPS5231420B1 (de) 1977-08-15
SE373731B (de) 1975-02-17
DE1793848B1 (de) 1980-04-30
DE1793842B1 (de) 1980-06-26
DE1793850C2 (de) 1980-12-11
NO134889B (de) 1976-09-27
DE1793842C3 (de) 1981-03-19
DE1793849C2 (de) 1982-07-01
DK139012B (da) 1978-12-04
DE1793845C2 (de) 1980-08-07
DE1793843C2 (de) 1981-01-15
DE1793850B1 (de) 1980-04-24
DE1793848C2 (de) 1981-01-15
ES326503A1 (es) 1967-07-01
JPS499746B1 (de) 1974-03-06
DE1793847B1 (de) 1980-06-26
DE1793846B1 (de) 1980-04-30
JPS4821509B1 (de) 1973-06-29
CH529516A (de) 1972-10-31
SE373736B (de) 1975-02-17
NO134889C (de) 1977-01-05
DE1793846C2 (de) 1981-01-15
DE1793844C2 (de) 1980-07-24
SE373734B (de) 1975-02-17
JPS5333667B1 (de) 1978-09-16
SE377270B (de) 1975-06-30

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